2-pentanone-5,5,5-d3 | 93278-91-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-pentanone-5,5,5-d3
• 英文别名: 5,5,5-Trideuteriopentan-2-one
• CAS: 93278-91-2
• 化学式: C₅H₁₀O
• 分子量: 89.11
• InChiKey: XNLICIUVMPYHGG-FIBGUPNXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  6
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  生成 2-pentanone-5,5,5-d3
  参考文献：
  名称：

  Characterization of five [C4H7O]+ Ion structures. Fragmentation of the 2-pentanone molecular ion

  摘要：

  AbstractThe [C4H70]+ ions [CH2CHC(OH)CH3]+ (1), [CH3CHCHC(OH)H]+ (2), [CH2C(CH3)C(OH)H]+ (3), [Ch3CH2CH2CO]+ (4) and [(CH3)2CHCO]+ (5) have been characterized by their collision‐induced dissociation (CID) mass spectra and charge stripping mass spectra. The ions 1–3 were prepared by gas phase protonation of the relevant carbonyl compounds while 4 and 5 were prepared by dissociative electron impact ionization of the appropriate carbonyl compounds. Only 2 and 3 give similar spectra and are difficult to distinguish from each other; the remaining ions can be readily characterized by either their CID mass spectra or their charge stripping mass spectra. The 2‐pentanone molecular ion fragments by loss of the C(1) methyl and the C(5) methyl in the ratio 60:40 for metastable ions; at higher internal energies loss of the C(1) methyl becomes more favoured. Metastable ion characteristics, CID mass spectra and charge stripping mass spectra all show that loss of the C(1) methyl leads to formation of the acyl ion 4, while loss of the C(5) methyl leads to formation of protonated vinyl methyl ketone (1). These results are in agreement with the previously proposed potential energy diagram for the [C5H10O]+˙ system.

  DOI：

  10.1002/oms.1210200108

文献信息

• The reactions of metastable [C5 H10 O]+˙ ions with the oxygen on the second carbon
  作者：David J. McAdoo、Charles E. Hudson、Fred W. McLafferty、Terry E. Parks

  DOI：10.1002/oms.1210190802

  日期：1984.8

  AbstractNearly all [C5H10O]+˙ isomers with the oxygen on the second carbon are shown to interconvert with each other and lose methyl and ethylene at the threshold for dissociation. The methyls contain the carbons from the 1‐ and 5‐positions with about equal frequency, and C(3) or perhaps C(4) about half as often as either terminal carbon. CH3 CH2 CH2 CO+ is formed by loss of the C(1) methyl and magnified image by loss of the C(5) methyl. Hydorgen transfer between C(5) and the oxygen and between the oxygen and C(4) are facile, and 1,2‐hydrogen transfers between C(3) and C(4) occur with high frequency. Extensive skeletal rearrangements also take placae by 1,2‐shifts between C(2), C(3) and C(4). We attribute the occurrence of teh three‐center shifts between C(2), C(3) and C(4) to the presence of considerable charge density on C(2) and C(3) in many of the [C5H10O]+˙ isomers. The isomerizations of [C5H10O]+˙ can be considered a mixture of free radical and carbocation reactions. Strong similarities exist between the isomerizations of metastable [C5H10O]+˙ ions with the oxygen on the second carbon and those of isomers of ionized butanoic acid, methyl butanoate and n‐butanal.
• Fragmentation reactions of the enolate ions of 2-pentanone
  作者：Allen Donnelly、Swapan Chowdhury、Alex. G. Harrison

  DOI：10.1002/oms.1210240206

  日期：1989.2

  AbstractThe reaction of [OH]− with 2‐pentanone produces two enolate ions, [CH3CH2CH2COCH2]− and [CH3COCHCH2CH3]−, by proton abstraction from C(1) and C(3), respectively. Using deuterium isotopic labelling the fragmentation reactions of each enolate have been delineated for collisional activation at both high (8 keV) and low (5–100 eV) collisional energies. The primary enolate ion fragments mainly by elimination of ethene. Two mechanisms operate: elimination of C(4) and C(5) with hydrogen migration from C(5), and elimination of C(3) and C(4) with migration of the C(5) methyl group. Minor fragmentation of the primary enolate also occurs by elimination of propane and elimination of C2H5; the latter reaction involves specifically the terminal ethyl group. The secondary enolate ion fragments mainly by loss of H2 and by elimination of CH4; for the latter reaction four different pathways are operative. Minor elimination of ethene also is observed involving migration of a C(5) hydrogen to C(3) and elimination of C(4) and C(5) as ethene.
• Characterization of five [C4H7O]+ Ion structures. Fragmentation of the 2-pentanone molecular ion
  作者：Keith R. Laderoute、Jan J. Zwinselman、Alex. G. Harrison

  DOI：10.1002/oms.1210200108

  日期：1985.1

  AbstractThe [C4H70]+ ions [CH2CHC(OH)CH3]+ (1), [CH3CHCHC(OH)H]+ (2), [CH2C(CH3)C(OH)H]+ (3), [Ch3CH2CH2CO]+ (4) and [(CH3)2CHCO]+ (5) have been characterized by their collision‐induced dissociation (CID) mass spectra and charge stripping mass spectra. The ions 1–3 were prepared by gas phase protonation of the relevant carbonyl compounds while 4 and 5 were prepared by dissociative electron impact ionization of the appropriate carbonyl compounds. Only 2 and 3 give similar spectra and are difficult to distinguish from each other; the remaining ions can be readily characterized by either their CID mass spectra or their charge stripping mass spectra. The 2‐pentanone molecular ion fragments by loss of the C(1) methyl and the C(5) methyl in the ratio 60:40 for metastable ions; at higher internal energies loss of the C(1) methyl becomes more favoured. Metastable ion characteristics, CID mass spectra and charge stripping mass spectra all show that loss of the C(1) methyl leads to formation of the acyl ion 4, while loss of the C(5) methyl leads to formation of protonated vinyl methyl ketone (1). These results are in agreement with the previously proposed potential energy diagram for the [C5H10O]+˙ system.